EP1026144B1 - Method of manufacturing an aromatic anti-bacterial agent containing hinokitiol - Google Patents
Method of manufacturing an aromatic anti-bacterial agent containing hinokitiol Download PDFInfo
- Publication number
- EP1026144B1 EP1026144B1 EP00101969A EP00101969A EP1026144B1 EP 1026144 B1 EP1026144 B1 EP 1026144B1 EP 00101969 A EP00101969 A EP 00101969A EP 00101969 A EP00101969 A EP 00101969A EP 1026144 B1 EP1026144 B1 EP 1026144B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hinokitiol
- bacterial agent
- aqueous solution
- agent containing
- manufacturing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 title claims description 70
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 title claims description 35
- 229930007845 β-thujaplicin Natural products 0.000 title claims description 35
- 239000003242 anti bacterial agent Substances 0.000 title claims description 19
- 125000003118 aryl group Chemical group 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 238000007654 immersion Methods 0.000 claims description 6
- 239000002023 wood Substances 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 description 21
- 230000000844 anti-bacterial effect Effects 0.000 description 11
- 239000003205 fragrance Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 230000033116 oxidation-reduction process Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000011946 reduction process Methods 0.000 description 4
- 230000000922 anti-bactericidal effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 208000037942 Methicillin-resistant Staphylococcus aureus infection Diseases 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 241001460074 Microsporum distortum Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 229910001260 Pt alloy Inorganic materials 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000218636 Thuja Species 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 229910001297 Zn alloy Inorganic materials 0.000 description 1
- 201000007691 actinomycosis Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006161 blood agar Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
Definitions
- This invention relates to a method of manufacturing an aromatic anti-bacterial agent with anti-bacterial and bactericidal effects containing hinokitiol as its principal ingredient.
- a variety of pathogenic and other bacteria may be found in our surroundings, i.e., in our everyday living spaces, and it is known that these bacteria may be killed or their growth may be prevented by the spraying or application of hinokitiol extracted from the hinoki (Japanese cypress), the thuja or the like.
- Hinokitiol is a substance produced via extraction from hinoki and can be used at no risk to humans or animals. It has been proven to have anti-bacterial and bactericidal properties and is also effective against ticks and mildew. Clinically, hinokitiol has been shown to be effective for patients with atopic dermatitis; it also functions against dermatophytosis, actinomycosis and the bacteria that cause athlete's foot, and further guards against and eliminates unpleasant odors.
- hinokitiol is aromatic anti-bacterial agents intended for interior use; hinokitiol is a principal ingredient in such agents.
- the scent of the hinokitiol can be overpowering to some.
- the hinokitiol has a powerful fragrance; if the solution adheres to the room's walls, furniture, etc., the fragrance can remain at undiminished strength for some time. If this fragrance is too strong, it cancels out other fragrances in the room (e.g., from flowers), resulting in an unattractive overall smell. Processing methods to reduce the strength of the fragrance are available; however, they have the undesirable effect of weakening the properties of the hinokitiol, and in particular, its usefulness as an anti-bacterial and bactericidal product.
- the object of this invention is to eliminate disadvantages mentioned above.
- a method of manufacturing an aromatic anti-bacterial agent containing hinokitiol in which an aqueous solution containing at least hinokitiol is extracted from wood chips, then reduced to produce an aromatic anti-bacterial agent.
- the extracted aqueous solution containing hinokitiol presents alkalinity when reduced, thus weakening the scent of the hinokitiol and enhancing the solution's bactericidal and anti-bacterial properties.
- the aromatic anti-bacterial agent obtained has a milder fragrance, even when applied to the skin, and does not give off a scent incompatible with its surroundings. Furthermore, the agent's enhanced anti-bacterial properties allow it to be used effectively against various types of dermatitis, etc.
- the reduction process can be carried out easily by immersing inert electrodes in the extracted aqueous solution until the oxidation-reduction potential declines to a predetermined level that is lower than at the start of immersion. Lowering the oxidation-reduction potential in this manner allows the reduction process to be controlled via the length of immersion time of the inert electrodes, thus simplifying the reduction process.
- the predetermined potential is a negative potential approximately 40 times or less that of the oxidation-reduction potential at the start of immersion.
- An aqueous solution containing hinokitiol is extracted by separating it from a solution containing a mix of oil and aqueous solution, obtained by directing high-pressure, high-temperature flow of steam at raw material comprised of wood fragments, e.g. hinoki chips, bark, branches or leaves, to fumigate the raw material, followed by rapid cooling and liquefaction of the steam containing the hinokitiol.
- the raw material comprised of wood fragments of hinoki is thus reduced to approximately sawdust-sized particles, which enhances extraction efficiency as by increasing the surface area of the overall supply of the raw material, i.e., the area available for contact with the steam.
- the solution extracted i.e. the undiluted extract
- This undiluted extract is accumulated in a container used for extraction, the oil is separated, and the aqueous solution is separated from the oil and placed in a separate vessel to obtain an aqueous solution containing at least hinokitiol.
- This aqueous solution may of course also contain other beneficial extracts apart from hinokitiol.
- the aqueous solution obtained is reduced.
- inert electrodes made from a material such as platinum are first immersed in the solution.
- the inert electrodes may be of a type in general use in the field of the art and consist for example of thin metal plates square in shape, of platinum/magnesium alloy, zinc alloy and copper alloy.
- the inert electrodes are positioned at a suitable distance from each other in parallel on the same axis. Immersing the inert electrodes in the aqueous solution causes oxidation-reduction potential to be generated on the inert electrodes. This oxidation-reduction potential decreases as the aqueous solution is reduced.
- the oxidation-reduction potential falls to a predetermined level which is a negative potential forty times or less the negative oxidation-reduction potential at the start of immersion.
- the inert electrodes When the inert electrodes have been left in the aqueous solution for some 24 hours, they are removed from the aqueous solution. This completes the reduction process used to obtain an aromatic anti-bacterial agent containing hinokitiol.
- an aqueous solution which is an aqueous part of the aromatic anti-bacterial agent from raw materials and which contains at least hinokitiol, the distinctive fragrance of hinokitiol can be lessened.
- the aromatic anti-bacterial agent also possesses enhanced anti-bacterial properties compared to solutions that have not been subject to reduction.
- Tables 1 and 2 show the results of trials conducted to evaluate the bactericidal ability of the aromatic anti-bacterial agent containing hinokitiol obtained by this method.
- the evaluation was conducted as follows: using the Phenol Coefficient Method, 5ml of aromatic anti-bacterial agent containing hinokitiol was inoculated with 0.1ml of 10 6 bacteria solution and the bacteria population measured over time at 20° C. In this evaluation experiment, the number of live bacteria was measured every one hour after commencing experiment. The initial number of bacteria was measured by inoculating 5ml of a phosphoric acid buffer solution (1/15M pH 7.2) with 0.1ml of bacteria solution.
- the bacteria stock used were Escherichia coli; bacteria stock number IFO-3972, Pseudomonas aeruginosa; IFO-12689, MRSA (Methicillin resistant Staphylococcus aureus; KB-1005 (MRSA)), and Enterococcus faecalis; IFO-12580.
- Media used were Mueller Hinton II and a sheep's blood agar culture (BBL).
- Table 1 shows the results of these evaluation trials of bactericidal ability, and Table 2 the results of a control experiment conducted for the purposes of comparison.
- (Results of trial) Bacterium Change in bacteria numbers over time Start 1hr-1 1hr-2 1hr-3 Average E-coli 5.1 x 10 5 2.7 x 10 2 3.3 x 10 2 3.6 x 10 2 3.2 x 10 2 Ps.aeruginosa 4.7 x 10 5 4.3 x 10 2 3.9 x 10 2 3.9 x 10 2 4.0 x 10 2 MRSA 5.6 x 10 5 10 or less 10 or less 10 or less 10 or less En.faecalis 5.0 x 10 5 2.6 x 10 5 3.9 x 10 5 2.3 x 10 5 2.9 x 10 5 Unit: CFU/ml (Results of control experiment) Bacterium Change in bacteria numbers over time Start 1hr-1 1hr-2 1hr-3 Average E-coli 5.1 x 10 5 5.1 x 10 5 5.1 x 10 5 5.1
- the aromatic anti-bacterial agent containing hinokitiol was therefore observed to possess excellent bactericidal and anti-bacterial capabilities.
- the distinctive fragrance of hinokitiol was milder than that given off by a raw, unprocessed version of the substance.
- This aromatic anti-bacterial agent containing hinokitiol can therefore be used in rooms on a regular basis without a hinokitiol fragrance permeating the room to an overpowering degree, and is also effective in protecting rooms against bacteria, and in removing bacteria.
- the agent is particularly effective against MRSA, killing off bacteria so efficiently that no growth is detected an hour after application, making it ideal for use in hospitals to effectively prevent MRSA infection.
- the fragrance of the aromatic anti-bacterial agent containing hinokitiol is not overpowering when used indoors, it can be inhaled without creating any sense of excessive concentration, providing the same calming effect in the home or in hospitals as breathing in forest air.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
This invention relates to a method of manufacturing an aromatic anti-bacterial agent
with anti-bacterial and bactericidal effects containing hinokitiol as its principal
ingredient.
A variety of pathogenic and other bacteria may be found in our surroundings, i.e., in our
everyday living spaces, and it is known that these bacteria may be killed or their growth may
be prevented by the spraying or application of hinokitiol extracted from the hinoki (Japanese
cypress), the thuja or the like.
Hinokitiol is a substance produced via extraction from hinoki and can be used at no risk
to humans or animals. It has been proven to have anti-bacterial and bactericidal properties
and is also effective against ticks and mildew. Clinically, hinokitiol has been shown to be
effective for patients with atopic dermatitis; it also functions against dermatophytosis,
actinomycosis and the bacteria that cause athlete's foot, and further guards against and
eliminates unpleasant odors.
There has been growing use of the properties of hinokitiol in recent years. One typical
application is aromatic anti-bacterial agents intended for interior use; hinokitiol is a
principal ingredient in such agents.
However, if an aqueous solution containing hinokitiol, as extracted from hinoki, is
employed without any processing or dilution, the scent of the hinokitiol can be overpowering
to some. In other words, when the extracted aqueous solution is used in undiluted form, the
hinokitiol has a powerful fragrance; if the solution adheres to the room's walls, furniture, etc.,
the fragrance can remain at undiminished strength for some time. If this fragrance is too
strong, it cancels out other fragrances in the room (e.g., from flowers), resulting in an
unattractive overall smell. Processing methods to reduce the strength of the fragrance are
available; however, they have the undesirable effect of weakening the properties of the
hinokitiol, and in particular, its usefulness as an anti-bacterial and bactericidal product.
The object of this invention is to eliminate disadvantages mentioned above.
In order to achieve this object, a method of manufacturing an aromatic anti-bacterial
agent containing hinokitiol is used, in which an aqueous solution containing at least
hinokitiol is extracted from wood chips, then reduced to produce an aromatic anti-bacterial
agent.
If the above process is followed, the extracted aqueous solution containing hinokitiol
presents alkalinity when reduced, thus weakening the scent of the hinokitiol and enhancing
the solution's bactericidal and anti-bacterial properties.
The aromatic anti-bacterial agent obtained has a milder fragrance, even when applied to
the skin, and does not give off a scent incompatible with its surroundings. Furthermore, the
agent's enhanced anti-bacterial properties allow it to be used effectively against various
types of dermatitis, etc.
The reduction process can be carried out easily by immersing inert electrodes in the
extracted aqueous solution until the oxidation-reduction potential declines to a
predetermined level that is lower than at the start of immersion. Lowering the oxidation-reduction
potential in this manner allows the reduction process to be controlled via the
length of immersion time of the inert electrodes, thus simplifying the reduction process.
The predetermined potential is a negative potential approximately 40 times or less that of
the oxidation-reduction potential at the start of immersion.
The following describes an embodiment of the invention.
An aqueous solution containing hinokitiol is extracted by separating it from a solution
containing a mix of oil and aqueous solution, obtained by directing high-pressure, high-temperature
flow of steam at raw material comprised of wood fragments, e.g. hinoki chips,
bark, branches or leaves, to fumigate the raw material, followed by rapid cooling and
liquefaction of the steam containing the hinokitiol. The raw material comprised of wood
fragments of hinoki is thus reduced to approximately sawdust-sized particles, which
enhances extraction efficiency as by increasing the surface area of the overall supply of the
raw material, i.e., the area available for contact with the steam.
The solution extracted, i.e. the undiluted extract, contains a mixture of oil and aqueous
solution containing hinokitiol. This undiluted extract is accumulated in a container used for
extraction, the oil is separated, and the aqueous solution is separated from the oil and placed
in a separate vessel to obtain an aqueous solution containing at least hinokitiol. This
aqueous solution may of course also contain other beneficial extracts apart from hinokitiol.
Next, the aqueous solution obtained is reduced. Specifically, inert electrodes made
from a material such as platinum are first immersed in the solution. The inert electrodes
may be of a type in general use in the field of the art and consist for example of thin metal
plates square in shape, of platinum/magnesium alloy, zinc alloy and copper alloy. The inert
electrodes are positioned at a suitable distance from each other in parallel on the same axis.
Immersing the inert electrodes in the aqueous solution causes oxidation-reduction potential
to be generated on the inert electrodes. This oxidation-reduction potential decreases as the
aqueous solution is reduced. Generally, if the inert electrodes are left in the aqueous
solution over a 24-hour period, the oxidation-reduction potential falls to a predetermined
level which is a negative potential forty times or less the negative oxidation-reduction
potential at the start of immersion. When the inert electrodes have been left in the aqueous
solution for some 24 hours, they are removed from the aqueous solution. This completes the
reduction process used to obtain an aromatic anti-bacterial agent containing hinokitiol.
By reducing in this way an aqueous solution which is an aqueous part of the aromatic
anti-bacterial agent from raw materials and which contains at least hinokitiol, the distinctive
fragrance of hinokitiol can be lessened. Such the aromatic anti-bacterial agent also
possesses enhanced anti-bacterial properties compared to solutions that have not been
subject to reduction.
Tables 1 and 2 show the results of trials conducted to evaluate the bactericidal ability of
the aromatic anti-bacterial agent containing hinokitiol obtained by this method. The
evaluation was conducted as follows: using the Phenol Coefficient Method, 5ml of aromatic
anti-bacterial agent containing hinokitiol was inoculated with 0.1ml of 106 bacteria solution
and the bacteria population measured over time at 20° C. In this evaluation experiment, the
number of live bacteria was measured every one hour after commencing experiment. The
initial number of bacteria was measured by inoculating 5ml of a phosphoric acid buffer
solution (1/15M pH 7.2) with 0.1ml of bacteria solution.
The bacteria stock used were Escherichia coli; bacteria stock number IFO-3972,
Pseudomonas aeruginosa; IFO-12689, MRSA (Methicillin resistant Staphylococcus aureus;
KB-1005 (MRSA)), and Enterococcus faecalis; IFO-12580. Media used were Mueller Hinton
II and a sheep's blood agar culture (BBL).
Table 1 shows the results of these evaluation trials of bactericidal ability, and Table 2
the results of a control experiment conducted for the purposes of comparison.
| (Results of trial) | |||||
| Bacterium | Change in bacteria numbers over time | ||||
| Start | 1hr-1 | 1hr-2 | 1hr-3 | Average | |
| E-coli | 5.1 x 105 | 2.7 x 102 | 3.3 x 102 | 3.6 x 102 | 3.2 x 102 |
| Ps.aeruginosa | 4.7 x 105 | 4.3 x 102 | 3.9 x 102 | 3.9 x 102 | 4.0 x 102 |
| MRSA | 5.6 x 105 | 10 or less | 10 or less | 10 or less | 10 or less |
| En.faecalis | 5.0 x 105 | 2.6 x 105 | 3.9 x 105 | 2.3 x 105 | 2.9 x 105 |
| Unit: CFU/ml |
| (Results of control experiment) | |||||
| Bacterium | Change in bacteria numbers over time | ||||
| Start | 1hr-1 | 1hr-2 | 1hr-3 | Average | |
| E-coli | 5.1 x 105 | 5.1 x 105 | 5.1 x 105 | 5.1 x 105 | 5.1 x 105 |
| Ps.aeruginosa | 4.7 x 105 | 4.7 x 105 | 4.7 x 105 | 4.7 x 105 | 4.7 x 105 |
| MRSA | 5.6 x 105 | 5.5 x 105 | 5.6 x 105 | 5.6 x 105 | 5.6 x 105 |
| En.faecalis | 5.0 x 105 | 5.0 x 105 | 5.0 x 105 | 5.0 x 105 | 5.0 x 105 |
| Unit: CFU/ml |
As is apparent from Table 1, bacteria populations of all types decreased over time. This
decrease was particularly marked in the case of MRSA, with no bacteria growth observed
after one hour. Furthermore, as the results of the control experiment in Table 2 indicate, no
change was observed in the numbers of any of the bacteria types after one hour. These
results therefore clearly demonstrate that the bacteria were killed by the aromatic anti-bacterial
agent containing hinokitiol.
The aromatic anti-bacterial agent containing hinokitiol was therefore observed to
possess excellent bactericidal and anti-bacterial capabilities. In addition, the distinctive
fragrance of hinokitiol was milder than that given off by a raw, unprocessed version of the
substance. This aromatic anti-bacterial agent containing hinokitiol can therefore be used in
rooms on a regular basis without a hinokitiol fragrance permeating the room to an
overpowering degree, and is also effective in protecting rooms against bacteria, and in
removing bacteria. The agent is particularly effective against MRSA, killing off bacteria so
efficiently that no growth is detected an hour after application, making it ideal for use in
hospitals to effectively prevent MRSA infection. Furthermore, because the fragrance of the
aromatic anti-bacterial agent containing hinokitiol is not overpowering when used indoors, it
can be inhaled without creating any sense of excessive concentration, providing the same
calming effect in the home or in hospitals as breathing in forest air.
Claims (3)
- A method of manufacturing an aromatic anti-bacterial agent containing hinokitiol, comprising the steps of extracting an aqueous solution containing at least hinokitiol from wood chips and reducing the aqueous solution extracted to produce the aromatic anti-bacterial agent.
- A method of manufacturing an aromatic anti-bacterial agent containing hinokitiol as described in claim 1, wherein the reducing step can be carried out by immersing inert electrodes into the aqueous solution extracted until the oxidization-reduction potential reaches a predetermined level lower than that at the start of immersion.
- A method of manufacturing an aromatic anti-bacterial agent containing hinokitiol as described in claim2, wherein the electrical potential is a negative potential approximately 40 times or less the oxidization-reduction potential at the start of immersion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11026138A JP3134068B2 (en) | 1999-02-03 | 1999-02-03 | Method for producing hinokitiol-containing aromatic antibacterial agent |
| JP2613899 | 1999-02-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1026144A1 EP1026144A1 (en) | 2000-08-09 |
| EP1026144B1 true EP1026144B1 (en) | 2003-11-12 |
Family
ID=12185203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00101969A Expired - Lifetime EP1026144B1 (en) | 1999-02-03 | 2000-02-01 | Method of manufacturing an aromatic anti-bacterial agent containing hinokitiol |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US6183748B1 (en) |
| EP (1) | EP1026144B1 (en) |
| JP (1) | JP3134068B2 (en) |
| DE (1) | DE60006432T2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3134068B2 (en) * | 1999-02-03 | 2001-02-13 | 株式会社トピックス | Method for producing hinokitiol-containing aromatic antibacterial agent |
| US6387417B1 (en) * | 1999-08-23 | 2002-05-14 | Kazuo Iwai | Bactericide against vancomycin resistant enterococcus |
| JP2003102373A (en) * | 2001-09-28 | 2003-04-08 | Jcs:Kk | Sterilization method of poultry meat |
| US20030100254A1 (en) * | 2001-11-29 | 2003-05-29 | Kazuo Iwai | Method of sterilizing mammal carcasses |
| US20050013882A1 (en) * | 2003-04-16 | 2005-01-20 | Jacques Owen | Phyto fluid |
| EP1698225A1 (en) * | 2003-12-25 | 2006-09-06 | Yoichi Yasukawa | Animal excrement treatment material and process for producing the same |
| US20060213448A1 (en) * | 2005-03-24 | 2006-09-28 | Yoichi Yasukawa | Disposal material for animal excretions and a manufacturing method therefor |
| JP2008105957A (en) * | 2006-10-23 | 2008-05-08 | Hyogo Prefecture | Method for extracting hinokitiol, hinokitiol-containing aqueous extract and antibacterial agent |
| KR101154043B1 (en) * | 2011-07-01 | 2012-06-07 | 주식회사 에코덤 | Pharmaceutical composition and food composition for preventing or improving gastro-intestinal motility disorder |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5985279A (en) * | 1982-11-08 | 1984-05-17 | Seiwa Kasei Kk | Preventing animal or plant from blackening or browning |
| DE4202964A1 (en) * | 1992-02-01 | 1993-08-05 | Wella Ag | HAIR AND BODY TREATMENT |
| JPH0789819A (en) | 1993-09-17 | 1995-04-04 | Jumoku Chushutsu Seibun Riyou Gijutsu Kenkyu Kumiai | Aromatic fungicide composition |
| JP3269737B2 (en) | 1994-08-31 | 2002-04-02 | 宇野醤油株式会社 | Food preservative and method for producing the same |
| JPH09136992A (en) | 1995-11-10 | 1997-05-27 | Sangi Co Ltd | Antimicrobial composition |
| JPH09143045A (en) | 1995-11-17 | 1997-06-03 | Kanebo Ltd | Cosmetic material |
| US5811114A (en) * | 1996-06-12 | 1998-09-22 | E-L Management Corp. | Stabilized hinokitiol and compositions containing same |
| JP3134068B2 (en) * | 1999-02-03 | 2001-02-13 | 株式会社トピックス | Method for producing hinokitiol-containing aromatic antibacterial agent |
-
1999
- 1999-02-03 JP JP11026138A patent/JP3134068B2/en not_active Expired - Fee Related
-
2000
- 2000-01-20 US US09/487,991 patent/US6183748B1/en not_active Expired - Fee Related
- 2000-02-01 EP EP00101969A patent/EP1026144B1/en not_active Expired - Lifetime
- 2000-02-01 DE DE60006432T patent/DE60006432T2/en not_active Expired - Fee Related
- 2000-10-12 US US09/686,075 patent/US6391347B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1026144A1 (en) | 2000-08-09 |
| JP3134068B2 (en) | 2001-02-13 |
| JP2000226301A (en) | 2000-08-15 |
| DE60006432D1 (en) | 2003-12-18 |
| US6183748B1 (en) | 2001-02-06 |
| DE60006432T2 (en) | 2004-08-12 |
| US6391347B1 (en) | 2002-05-21 |
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